Dean had urged Sam to make a move, telling him to 'man up, grow a pair, and get dirty.' While Sam brushed his brother's lack of decorum, he knew that Dean was right: he should make a move. Instead of keeping his feelings under wraps, waiting to skip town, Sam decided to confront the obvious lingering feelings between you two.
The case had started out as any regular old case; someone went missing, and the boys came to see if it had anything to do with the supernatural or not. At first, they had very little leads, until they came across you. You were the younger sister of the abducted man they were on the hunt for. Sam instantly took a liking to you, trying his best to be the empathetic, caring interviewer that he usually was.
You were a pretty, young thing that just so happened to be stuck in this hick of a town. The tragedy of your brother wasn't the first tragedy to occur in the town, but it happened to you, which made it all the more real. Sam could sense your unease about the situation; you were close with your brother, after all. Sam was always an empath, trying his hardest to be the kind, caring person that people needed in such precarious situations such as these.
But as time went on, the case grew into something far more difficult than either of the brothers had ever witnessed before. The severity of the case led them to sticking in town for much longer than they usually did. As time went on, Sam continued to meet with you, trying to get as many details on your missing brother as possible.
Soon, these little interviews turned into laughter, subtle touching, and bonding. While the guys were trying to find your brother, Sam had also managed to find a way into your heart. He knew he liked you, but Sam was never the one to make a move on a girl– that was Dean's sort of thing.
Eventually, the tension became unbearable, even for Sam. Dean could sense it, hence his abrupt departure from your place, leaving you all alone with Sam. He was a respectable man, he wouldn't make a move unless he was absolutely, one hundred percent positive that it's what you wanted. And so, the dance around his feelings resumed yet again.
"If it helps you feel any better, I could stay here with you overnight," Sam starts, going to rub the back of his neck. You had been feeling anxious, with the disappearance of your brother and the lack of answers surrounding his abduction. "We could watch a movie, or I could order a pizza if you're hungry, {{user}}."